JPS61145188A - 含ケイ素イソシアネ−ト化合物の製造方法 - Google Patents
含ケイ素イソシアネ−ト化合物の製造方法Info
- Publication number
- JPS61145188A JPS61145188A JP26546884A JP26546884A JPS61145188A JP S61145188 A JPS61145188 A JP S61145188A JP 26546884 A JP26546884 A JP 26546884A JP 26546884 A JP26546884 A JP 26546884A JP S61145188 A JPS61145188 A JP S61145188A
- Authority
- JP
- Japan
- Prior art keywords
- group
- silicon
- formula
- carbonyl chloride
- toluene
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 229910052710 silicon Inorganic materials 0.000 title claims abstract description 11
- 239000010703 silicon Substances 0.000 title claims abstract description 11
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 title claims abstract description 9
- 239000012948 isocyanate Substances 0.000 title description 9
- -1 isocyanate compound Chemical class 0.000 title description 9
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims abstract description 16
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 11
- 150000003512 tertiary amines Chemical class 0.000 claims abstract description 8
- 150000003973 alkyl amines Chemical class 0.000 claims abstract description 6
- 239000003960 organic solvent Substances 0.000 claims abstract description 6
- 125000004469 siloxy group Chemical group [SiH3]O* 0.000 claims abstract description 4
- 239000000126 substance Substances 0.000 claims 2
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 abstract description 51
- 150000001875 compounds Chemical class 0.000 abstract description 11
- 239000002994 raw material Substances 0.000 abstract description 4
- 238000007086 side reaction Methods 0.000 abstract description 4
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 abstract description 4
- 150000002430 hydrocarbons Chemical group 0.000 abstract description 3
- WYTZZXDRDKSJID-UHFFFAOYSA-N (3-aminopropyl)triethoxysilane Chemical compound CCO[Si](OCC)(OCC)CCCN WYTZZXDRDKSJID-UHFFFAOYSA-N 0.000 abstract description 2
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 abstract description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 abstract 2
- 238000006243 chemical reaction Methods 0.000 description 13
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- 238000000034 method Methods 0.000 description 12
- 239000000243 solution Substances 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 239000013078 crystal Substances 0.000 description 8
- 150000002513 isocyanates Chemical class 0.000 description 7
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 238000009835 boiling Methods 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- WOAZEKPXTXCPFZ-UHFFFAOYSA-N dimethyl(phenyl)azanium;chloride Chemical compound Cl.CN(C)C1=CC=CC=C1 WOAZEKPXTXCPFZ-UHFFFAOYSA-N 0.000 description 3
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 3
- KYZSFZRRZVYDDA-UHFFFAOYSA-N 1,5-dimethylcyclohexa-2,4-dien-1-amine Chemical compound CC1(N)CC(=CC=C1)C KYZSFZRRZVYDDA-UHFFFAOYSA-N 0.000 description 2
- OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 2
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 2
- GGSUCNLOZRCGPQ-UHFFFAOYSA-N diethylaniline Chemical compound CCN(CC)C1=CC=CC=C1 GGSUCNLOZRCGPQ-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- GTCAXTIRRLKXRU-UHFFFAOYSA-N methyl carbamate Chemical compound COC(N)=O GTCAXTIRRLKXRU-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 1
- 229910021604 Rhodium(III) chloride Inorganic materials 0.000 description 1
- 238000007259 addition reaction Methods 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- HXBPYFMVGFDZFT-UHFFFAOYSA-N allyl isocyanate Chemical compound C=CCN=C=O HXBPYFMVGFDZFT-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-N carbonic acid monoamide Natural products NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 239000007822 coupling agent Substances 0.000 description 1
- HPYNZHMRTTWQTB-UHFFFAOYSA-N dimethylpyridine Natural products CC1=CC=CN=C1C HPYNZHMRTTWQTB-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000003365 glass fiber Substances 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 238000010422 painting Methods 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229920006267 polyester film Polymers 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- SONJTKJMTWTJCT-UHFFFAOYSA-K rhodium(iii) chloride Chemical compound [Cl-].[Cl-].[Cl-].[Rh+3] SONJTKJMTWTJCT-UHFFFAOYSA-K 0.000 description 1
- 150000003377 silicon compounds Chemical class 0.000 description 1
- 125000005353 silylalkyl group Chemical group 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- KJAMZCVTJDTESW-UHFFFAOYSA-N tiracizine Chemical compound C1CC2=CC=CC=C2N(C(=O)CN(C)C)C2=CC(NC(=O)OCC)=CC=C21 KJAMZCVTJDTESW-UHFFFAOYSA-N 0.000 description 1
- CMMXCVYESRODNH-UHFFFAOYSA-N trichloroepoxyethane Chemical class ClC1OC1(Cl)Cl CMMXCVYESRODNH-UHFFFAOYSA-N 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP26546884A JPS61145188A (ja) | 1984-12-18 | 1984-12-18 | 含ケイ素イソシアネ−ト化合物の製造方法 |
| DE19853544601 DE3544601A1 (de) | 1984-12-18 | 1985-12-17 | Verfahren zur herstellung von siliciumhaltigen isocyanatverbindungen |
| FR858518711A FR2574796B1 (fr) | 1984-12-18 | 1985-12-17 | Procede de preparation de composes d'isocyanate contenant du silicium |
| US06/810,314 US4654428A (en) | 1984-12-18 | 1985-12-17 | Process for preparation of silicon-containing isocyanate compounds |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP26546884A JPS61145188A (ja) | 1984-12-18 | 1984-12-18 | 含ケイ素イソシアネ−ト化合物の製造方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS61145188A true JPS61145188A (ja) | 1986-07-02 |
| JPH058713B2 JPH058713B2 (enrdf_load_stackoverflow) | 1993-02-02 |
Family
ID=17417585
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP26546884A Granted JPS61145188A (ja) | 1984-12-18 | 1984-12-18 | 含ケイ素イソシアネ−ト化合物の製造方法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS61145188A (enrdf_load_stackoverflow) |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH01275587A (ja) * | 1988-04-26 | 1989-11-06 | Shin Etsu Chem Co Ltd | 含ケイ素イソシアネート化合物の製造方法 |
| US4880927A (en) * | 1986-12-03 | 1989-11-14 | Shin-Etsu Chemical Co., Ltd. | Method for preparing a cyclic isocyanuric ester having organosilicon groups |
| JPH02236089A (ja) * | 1989-01-25 | 1990-09-18 | Festo Kg | 接続具 |
| JPH06228161A (ja) * | 1993-01-29 | 1994-08-16 | Shin Etsu Chem Co Ltd | イソシアネート基含有オルガノポリシロキサンの製造方法 |
| JP2007333107A (ja) * | 2006-06-15 | 2007-12-27 | Sakura Gomme Kk | 結合金具 |
| JP2010013463A (ja) * | 2001-08-06 | 2010-01-21 | Evonik Degussa Gmbh | 有機珪素化合物、その製造法、該化合物を含有するゴム混合物および該化合物の使用 |
| JP2015521200A (ja) * | 2012-05-29 | 2015-07-27 | モメンティブ パフォーマンス マテリアルズ ゲーエムベーハー | イソシアナートシランの作製 |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP5336447B2 (ja) | 2010-09-02 | 2013-11-06 | 日立建機株式会社 | 電気駆動車両 |
| JP6237611B2 (ja) | 2014-12-24 | 2017-11-29 | 信越化学工業株式会社 | イソシアネート基含有有機ケイ素化合物、その製造方法、接着剤、粘着剤およびコーティング剤 |
-
1984
- 1984-12-18 JP JP26546884A patent/JPS61145188A/ja active Granted
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4880927A (en) * | 1986-12-03 | 1989-11-14 | Shin-Etsu Chemical Co., Ltd. | Method for preparing a cyclic isocyanuric ester having organosilicon groups |
| JPH01275587A (ja) * | 1988-04-26 | 1989-11-06 | Shin Etsu Chem Co Ltd | 含ケイ素イソシアネート化合物の製造方法 |
| JPH02236089A (ja) * | 1989-01-25 | 1990-09-18 | Festo Kg | 接続具 |
| JPH06228161A (ja) * | 1993-01-29 | 1994-08-16 | Shin Etsu Chem Co Ltd | イソシアネート基含有オルガノポリシロキサンの製造方法 |
| JP2010013463A (ja) * | 2001-08-06 | 2010-01-21 | Evonik Degussa Gmbh | 有機珪素化合物、その製造法、該化合物を含有するゴム混合物および該化合物の使用 |
| JP2007333107A (ja) * | 2006-06-15 | 2007-12-27 | Sakura Gomme Kk | 結合金具 |
| JP2015521200A (ja) * | 2012-05-29 | 2015-07-27 | モメンティブ パフォーマンス マテリアルズ ゲーエムベーハー | イソシアナートシランの作製 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH058713B2 (enrdf_load_stackoverflow) | 1993-02-02 |
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